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forget about trying to carry all your luggage in the cabin unless you are going somewhere for only a couple of days and dont need to take much, toothbrush , clean jocks, laptop.
buy yourself a backpack that has a day pack which clips securely too it, also make sure the straps can be tucked away ie dont dangle loosely to get caught on conveyors, greasy trolley pins etc. when packing put those valuables you cant carry on your person, in the day pack, plus a change of underwear & toothbrush so that if your main pack does get lost you have all you need to be comfortable overnight or until it is recovered. (i've had baggage lost a couple times in 30years of backpacking, but it has always turned up within 24hours.) take the day pack in the cabin.
as for the carry on luggage being below acceptable size, wear as much clothing as possible when checking in, and take it off when you get on the plane. be modular, if they are going to stop you because your baggage is over size, be prepared to change it there and then. i've never seen anyone refused boarding because they have had too many clothes on, you'd be surprised how much gear you can shove in jacket pockets etc.
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